914225-70-0 | 5'-fluoro-2'-Iodoacetophenone

CAS:914225-70-0 | 5'-fluoro-2'-Iodoacetophenone,Description

5’-Fluoro-2’-iodoacetophenone, also known as 1-(5-Fluoro-2-iodophenyl)ethanone, is a chemical compound with the CAS number 914225-70-0. It is used as a pharmaceutical intermediate. It is a key intermediate in the synthesis of a next-generation small-molecule inhibitor of the orphan receptor tyrosine kinase c-ros oncogene 1 (ROS1), which is used in the treatment of various types of cancer.

Synthesis Analysis

The synthesis of 5’-Fluoro-2’-iodoacetophenone involves several steps. The process starts with 2-amino-5-fluorobenzoic acid, which is mixed in a sulfuric acid solution. Sodium nitrite is then added, and the mixture is stirred until no solid remains. Urea is added, followed by a solution of potassium iodide. The resulting brown solid is dissolved in ethyl acetate and washed with hydrochloric acid, sodium bisulfate, and saturated salt water to obtain 5-fluoro-2-iodobenzoic acid.

Molecular Structure Analysis

The molecular formula of 5’-Fluoro-2’-iodoacetophenone is C8H6FIO. Its molecular weight is 264.04 g/mol.

Physical And Chemical Properties Analysis

5’-Fluoro-2’-iodoacetophenone is a brown liquid. It is slightly soluble in water. It has a predicted boiling point of 269.5±25.0 °C. It is sensitive to light and should be stored in a dark place.

Scientific Research Applications

• Synthesis of Fluorinated Compounds : 5-Fluoro-2-hydroxyacetophenone, a related compound, is synthesized from p-aminophenol, which is a process involving esterification, Fries rearrangement, hydrolysis, and fluorine diazotization. This method could potentially be applicable to 5'-Fluoro-2'-iodoacetophenone as well (Zhao Xiang-kui, 2009).
• Comparative Imaging Studies : The synthesis of a benzophenone-based labeling compound, which can be labeled with either F-18 or iodine radioisotopes, indicates the potential of using 5'-Fluoro-2'-iodoacetophenone derivatives in imaging studies, particularly in positron emission tomography (PET) and single-photon computed tomography (SPECT) (Zizhong Li et al., 2003).
• Chemotherapy Research : Related compounds like 5-Fluorouracil (5-FU) have been used in cancer treatment. Understanding of its mechanism has led to strategies enhancing its anticancer activity, which might provide insights for the application of 5'-Fluoro-2'-iodoacetophenone in similar contexts (D. Longley, D. Harkin, P. Johnston, 2003).
• Electrochemical Applications : Electrochemical conversion of haloacetophenones, which includes compounds similar to 5'-Fluoro-2'-iodoacetophenone, to corresponding alcohols indicates its potential use in electrochemical applications (Y. Ikeda, 1990).
• Antibiotic Synthesis : The synthesis of nucleoside antibiotics like nucleocidin, which involve fluorinated compounds, suggests possible roles for 5'-Fluoro-2'-iodoacetophenone in antibiotic development (I. D. Jenkins, J. Verheyden, J. G. Moffatt, 1976).
• Analytical Chemistry : Studies on iodination of fluorinated benzonitriles, including the synthesis and analysis of fluorinated compounds, could extend to the analysis and manipulation of 5'-Fluoro-2'-iodoacetophenone (Anna L. Dunn et al., 2018).
• Cancer Chemotherapy : Clinical applications of fluorinated pyrimidines like 5-FU in cancer chemotherapy offer insights into the potential therapeutic applications of 5'-Fluoro-2'-iodoacetophenone and its derivatives (C. Heidelberger, F. Ansfield, 1963).
• Pharmaceutical Synthesis : The synthesis of complex compounds involving fluorine-substituted acetophenone derivatives, like 5'-Fluoro-2'-iodoacetophenone, has potential applications in the development of new pharmaceuticals (Liang‐Zhong Xu et al., 2004) .
• Development of Anti-inflammatory Agents : The synthesis and biological evaluation of fluorine-substituted chalcone derivatives, which are structurally related to 5'-Fluoro-2'-iodoacetophenone, for their anti-inflammatory and analgesic properties suggest similar potential applications for 5'-Fluoro-2'-iodoacetophenone (Khaled R. A. Abdellatif et al., 2015).

Safety And Hazards

5’-Fluoro-2’-iodoacetophenone is classified as a skin irritant (Category 2), an eye irritant (Category 2), and may cause respiratory irritation (Category 3). It should be handled with care, avoiding contact with skin and eyes, and not be inhaled. It should be stored in a well-ventilated place and kept in a tightly closed container.

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